Journal of Applied Polymer Science, Vol.56, No.9, 1127-1131, 1995
Solid-Phase Peptide-Synthesis on a Novel Hydrogenolysable Linker-Resin Combination
The propensity of benzyloxycarbonylamide group towards clean and rapid hydrogenolysis was exploited in designing a linker for solid phase peptide synthesis on a copoly(styrene-divinylbenzene) resin support. Hydroxymethyl copoly(styrene-divinylbenzene) on treatment with 4-nitrophenyl chloroformate gave a resin which possessed benzyl 4-nitrophenyl carbonate pendants. These reacted with the a-amino group of Boc-Lys-OMe, resulting in the attachment of the latter through its side chain to the resin by a benzyloxycarbonylamide linkage. This was used to extend the peptide chain from the alpha-amino end of lysine by Boc-methodology. The peptide was released from the resin through palladium acetate-ammonium formate-based transfer hydrogenolysis. The usefulness of this linker was demonstrated by synthesizing several small peptides terminating in lysine.